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15 Unusual Online Dating Questions to Ask a Guy Before Meeting Him For the First Time



Getting to know someone or being in a relationship with them is not a one day task. You need to unfold various layers of a person’s behaviour, ethics, beliefs, personality to know about a person.

But asking straight forward questions might not seem right and can be rude. So here are some unusual questions that can be asked while dating a guy online which can in a way help to get to know deeply about that person.


What’s the stupidest thing you have done?

Asking this question to your guy can make him indulge in a light-hearted conversation. It can slowly open him up and he will become comfortable with you and you will come to know about him fun frolic side.


Play rapid-fire with him

This can actually be a mind-blowing game. you can get to know important things about your guy making both easy with each other. It will always sway away all your hesitations.

This game goes with very simple rules. You ask him one-word questions and he will have to answer within seconds, using one adjective or a name that comes to his mind instantly.

This can be a good way to know what are his thought processes.


What the best outfit that you have worn

Usually, you cannot directly ask what is his clothing sense. But asking an indirect question will not make him offended, rather he will happily describe what was his best outfit.

This will show how he presents himself in front of others and how important is it for him to be dressed up properly.


To what limits can you go to save your best friend?

This will reveal his emotional connection to people. If he is social and likes to connect with people, he’ll definitely have a million of stories to share with you and will go on and on.

This will show how people are close to him and how important it is for him to save his near and dear ones.


What’s your most expensive purchase?

By answering this question, a guy will tell a lot about how he manages his expenses and how smartly he invests money. Is he a spendthrift or a stingy person. You’ll get to know about it


How do you deal with praises and compliments?

This question will show how open he is and how he tackles those compliments and praises. This will make know about how nicely the guy is accepted in the society and how much he is liked by the people.


What’s your best childhood memory?

This question will make you know what bond he shares with his family and how he gets along with them This can be a good way to know about his personal life. If he’s happy sharing his memories with you, then he definitely has a good relation at home and is happy with his family.


Ask about his tastes and preferences.

You can know whether you two can get along or do you have any commonalities when it comes to food. Because people sharing the same liking usually tend to have a good bond.


What are you good at or do you have any special talents?

This question will tell a lot about a guys skills and talents. Girls are attracted to guys who are good in recreational activities. It would be even better if you share some common talent.


How would you celebrate your 50th wedding anniversary?


This will make you know a lot about how he is or will be handling his relationship. The more he describes the picture of how it should be, the more he is into giving efforts and time when in a relationship.


What boosts you up?

Knowing about what boosts him up, lets you know what are he is more inclined to, and what makes him feel good.


An evening show or a basketball match?

A very debatable question that is!

But you need to know a guy’s priority when it comes to a match or a show, what he prefers. This will show whether he will put your wishes first or his match.


What would you have become instead of what you are doing right now?


A persons interest and career usually don’t match. So you can get to know a little bit more about his aspirations and dreams and what he liked the most and what he wanted to pursue.


What’s your idea of a perfect day?

This can be an interesting point to have a great and a long conversation, where you get to know each others liking and what is his “must-haves” for a perfect day.


What are your expectations of your partner?

This question can be intriguing. This will make the guy reply carefully because this will have an impression on the girl, which will make the girl know what kind of expectations she will have to stand up to if they date.


At last, getting to know a person can be the most beautiful experience ever, and its a cherry on the top when you meet a genuine person in your life.


No matter what mode you choose to converse but what matters is that you have a lot to talk about. You should never run out of conversations. After these, it is solely your decision whether you want to take it further or not.


Up Next: Can Jealousy Be Positive? Explore the Healthy Side of Jealousy & Open New Opportunities For You.


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